The Best Mistakes I've Made: Ex-Idealog editor Matt Cooney on why 'you're only as good as your next venture'

Idealog has partnered with Callaghan Innovation to take a look at the nature of failure in business – the good, the bad and the unintentionally educational. So we’re asking questions: Is there a stigma, in this country, around ‘failure’? Is it a good thing to ‘fail fast’? Would you be wary investing in a start-up run by an entrepreneur with a string of failed businesses? We’ll be presenting the results of our survey in a special feature – ‘The F Word’ – in the next issue of Idealog. In the lead up to that, we’re asking Kiwi high-fliers and heavy-hitters about what failure means to them, what they’ve learned, and what ‘mistakes’ they’re most proud of.

Here's what Matt Cooney, Idealog's editor from 2005 to 2011, had to say about the subject in an editorial back in 2011.

Ten years ago I was leading the development team at a well-funded tech startup. We had a lot going for us: a decent track record, a talented team with some genuine superstars and an existing revenue stream. We were ambitious and we had a brilliant business plan that just couldn’t go wrong.

As you’ve already worked out, dear reader, this venture failed, and the sometimes starry-eyed investors who stuck with the company eventually sold their stake for about one-twentieth of their investment.

The reasons are complex, but unremarkable. Failure is the constant companion of entrepreneurs, risk-takers and dreamers. Those who deal with it best are perhaps those most likely to succeed, and those who haven’t made mistakes probably haven’t made anything.

Mistakes certainly don’t faze Rowan Simpson. You might think it shouldn’t: Simpson was an early employee and shareholder at Trade Me and cashed up when Fairfax bought the little auction site. He had an early strategic and investment role at über-startupXero, and now spends his time consulting and investing through his own investment vehicle.

Rowan writes frankly about his Trade Me and investing experience. It’s a must-read for anyone in or planning a tech startup, but it’ll be enlightening for all Idealog readers. Even for serially successful people, mistakes and missteps—sometimes fatal, sometimes fortuitous—are facts of life. It’s often only in retrospect that we know what we got right and what we got wrong.

Geoff Matthews would understand. He has a simple formula: find companies with great products that are under-performing and give them a serious dose of capital, business smarts and, most importantly, ambition. It’s not always the Kiwi way, he tells Vincent Heeringa. “As a consultant I became frustrated that we’d suggest all these ways to grow businesses but the owners would shelve the idea because they couldn’t implement them. It’s such a common story in New Zealand—we’d see all these great ideas and ask, ‘What’s stopping you?’ Capital and courage? Well, that’s easy to fix.”

That includes courage to look beyond mistakes and see the big picture. That decade-old failure still rankles sometimes, but the former staff have gone on to great things in great companies and their own startups. Truth is, you’re only as good as your next venture.